If you want to HotSync your Palm with your PowerBook, the easiest and most tangle-free way of doing it is with Infrared. To make things go smoothly make sure you are using the latest versions of the software:

Palm OS 3.3 includes the libraries for the Palm side, and Mac OS 8.6 includes the libraries or the Mac side. Here’s checklist of things to check on the Mac side:

Go to Control Panels -> Infrared and make sure you have IrDA selected. You need a PowerBook with IrDA capability (which rules out the 5300 series) to do this.

Make sure AppleTalk isn’t using Infrared.

In the HotSync Setup (HotSync Manager -> HotSync -> Setup), click on the serial port settings tab and select Infrared port for the Local Setup.

Make sure HotSync is enabled in the HotSync Controls tab.

On your Palm, launch the HotSync app, select IrComm for the port, and click on the big HotSync button.

Point your Palm’s Infrared port at your PowerBook’s Infrared port, making sure they’re at least a few inches away from each other

HotSyncing should start within a few seconds. If it doesn’t just cancel on the Palm side and try again.

I’ve HotSync’ed hundreds of times with my PowerBook without any problems. The connection works best when you don’t move either unit after you’ve got a connection. Place them both on a table and don’t touch them.

Also, after a HotSync, you might notice the Palm seems to be waiting for another Palm to beam it information. I usually just remove the Palm from the IR range and press cancel on it.